


Lose It

by haikuhamster



Category: Supernatural
Genre: Barebacking, Begging, Bottom Dean, Cock Slut Dean, Dirty Talk, Dom/sub Undertones, First Time, First Time Bottoming, M/M, Plot What Plot/Porn Without Plot, Porn Star Castiel, Porn Star Dean Winchester, Rimming, Rough Sex, Top Castiel, don't look at me okay, i'm too soft not to include fluff
Language: English
Status: Completed
Published: 2018-08-18
Updated: 2018-08-18
Packaged: 2019-06-29 07:38:46
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 8,914
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/15724929
Author URL: https://archiveofourown.org/users/haikuhamster/pseuds/haikuhamster
Summary: There are two things Dean knows for certain: Bert and Ernie are gay, and he's not a bottom.Somehow, the universe seems to think he's wrong. He'll just have to prove it, in that case. He's not gonna like bottoming at all, that's for sure. Not one bit....It's way more than one bit.





	Lose It

**Author's Note:**

> THIS HAS BEEN COMING FOR SO LONG. I AM FINALLY DONE WITH THIS. AAAAAA!
> 
> Love and hugs to [RavensCAT](https://archiveofourown.org/users/RavensCAT/pseuds/RavensCAT) for beta reading this and yelling at me to write this, to [Adaille](https://archiveofourown.org/users/adaille/pseuds/adaille) for yelling at me to write this way more than anyone else, and [ThePornFairy](https://archiveofourown.org/users/ThePornFairy) for providing me with way too many inspiring gifs. You're all wonderful.
> 
> Warning: The first two paragraphs (excluding dialogue) are explicit Dean/Other, just some random dude who gets no description and is not at all important. You can skip it if you want, though.

“Oh fuck, I’m gonna come. I’m gonna come.”

“Ah, yeah. Do it.”

Dean thrust his hips hard and fast as the guy under him jacked himself wildly. Cum streaked across the dude’s stomach and fist and they groaned together, Dean gently rocking in and out of him. He had to admit, this wasn’t the greatest fuck he’d ever had. He was, though, obliged to make it seem like he was having the time of his life. He was a gentleman, after all.

“So hot, baby,” Dean grunted. He thrust into the guy’s ass a few more times, pulling out once he got close. He played his noises up a bit as he jerked his cock, and his partner moaned too, moaned like he really wanted Dean to come all over his ass. The thought was good, and Dean used it to push himself over the edge. He stepped forward and watched as streaks of white shot from him and covered the other man’s lube-wet hole. It wasn’t nearly as hot as coming inside of someone, but that wasn’t what had been planned for this specific interaction. When the last tremors finished he dropped down over the guy, stumbling into a sloppy kiss that was mostly just their tongues lazily sliding together and the two of them panting into each other’s mouths.

“Cut!” Gabriel yelled, and Dean immediately pulled away from the guy below him. “That’s a wrap, everyone. Nice work, boys. Nailed it, pun fully intended.”

The guy grunted and sat up, stretching his muscles as he lifted himself off the bed. “Nice work,” he said, likely just a courtesy.

“You too,” Dean said, though really it wasn’t. He knew he was shitty in that scene, but whatever. It was low-budget filler, just two dudes fucking with no chemistry whatsoever. It was catered to an audience of people who were just into the porn for dicks in butts, nothing else. Hell, there wasn’t even any foreplay. They’d just gone from dressed to undressed to kissing to boning. Dean didn’t even know the guy’s porn-name, let alone his real name.

He walked off the set, not caring about his nudity. It was quite literally his job not to give a fuck about the fact that his junk was going to be seen by people he might not want seeing it otherwise. May as well go all in.

It’s not like Dean wasn’t attractive. He _knew_ he was hot. Plus, he had the notches in his belt to prove it, even outside of porn. He was a damn good lay too. He didn’t go for women much anymore; he liked the tightness of the body with the firmness of the muscle. He could find buff chicks if he wanted, but toned dudes were more plentiful. Dudes were often better at sucking cock and giving handjobs anyway. And he never had to worry about some Harry-Met-Sally fake orgasm thing.

This job did have its perks, for sure. It gave him some definite hook-up points. When someone asked what he did he would give his token grin and say, “I’m a pornstar.” Nine times out of ten, they’d salivate over him. He loved sex, he needed the money, and Gabriel wasn’t too sleazy. Plus, the studio specialized in bareback, so he could indulge himself and not worry about diseases. Rigorous testing was quite a pro, here.

“Michael,” Gabriel called. Dean spun around and met the man’s eyes. “Shower quick, I gotta talk to you about something.” Dean grinned when he saw the spark in Gabe’s eyes. Last time he had that look, Dean had been set up with a twink and a bear, and they spit roasted the kid. Still one of the hottest scenes he’d ever done. Dean shot out an affirmative and strutted a little quicker to the showers. 

He was washed, dried and dressed in fifteen minutes. He made his way to Gabe’s office and let himself in, knowing he didn’t really give a shit. Sure enough, Gabriel was smiling at him while Dean sat down in the chair across from him. “You rang?” Dean said by way of greeting.

“That I did,” Gabriel confirmed. “I had a little idea come to me and I was hoping you’d be interested? You seem to be pretty diligent in trying new things.”

Dean grinned. “I’ll try anything once.”

“That’s what I like to hear,“ Gabe praised. “Now, you only top in scenes. We never specified anything from the get-go, but based off your early roles I kinda figured. Am I correct?” Dean nodded. “Good. Now, you just reached 50000 subscribers. I was thinking you could thank them with a video of you bottoming.”

Shock washed over Dean entirely, shorting his brain out. _What?_

“It’s not a big deal,” Gabe continued, clearly not aware of Dean’s surprise. “It won’t be too different in porn than it is in real life, and I even have a top picked out for you. He’s one of the best we got. I mean, god, he’s up there with you as far as tops go. Absolutely legendary. You down?”

Dean forced his brain to speak. “Uh, I’m not,” he spluttered. “I don’t, uh. I don’t bottom.”

“Oh, is it like…” Gabriel trailed off, a sympathetic wince overtaking his face, and it took a second for Dean to realize what he was talking about.

“No!” he said. “No, I was never- never, uh, assaulted. No trauma or anything, I just… Haven’t. It’s not really my style.”

Gabriel’s eyes widened, and the humor returned to his face. “Really? Ass like yours?”

Dean rolled his eyes. “Yeah, no, nothing.”

“What about fingers?” Gabe asked. “Ever try a little…” He pointed one finger up and wiggled it around a bit.

“No,” Dean said, exasperated. “Nothing’s ever gone in there and I never really planned on changing that.”

“So you’re nixing it? Just like that?” Gabriel raised an eyebrow and leaned forward, getting into businessman-mode. “This is 50k subs we’re talking about, Dean. It’s a big moment.”

“I mean, yeah,” he agreed. “It is. I’ve been doing this for a couple years and now I… yeah. It’s an accomplishment.” He paused, gathering his thoughts. “I wouldn’t come so far without the fans I have, so I guess they deserve something. But that’s bigger than 50k.”

Gabriel nodded, very obviously putting some things together in his head. “Alright. How about 60?” Dean shook his head. “75?”

He hesitated, then sighed. “I’ll think about 75. But don’t get your hopes up yet. Don’t tell anyone, don’t campaign. Nada.”

“Absolutely,” Gabriel agreed. “Despite the fact that I’m clearly pressuring you a bit, I want you to think about this and come to me with a decision. Nothing happens without your explicit consent, ever. That goes for topping, bottoming, whatever. You will always have a choice and no matter how disappointed I am, I’m always gonna respect it.”

Dean smiled. That reminder did help to make him feel marginally more secure. “I know,” he said. “You’ve got my back. I’ll let you know once I’ve thought about it.”

 

•°•°•°•°•°•°•°•

 

As it turned out, Dean didn’t need too long to think about it. The next day, he reached a decision. He looked at his subscriber count, that awesome little “50.6k” a sweet little reminder that this was important to people and he could get through it. Besides, it wasn’t a big deal. It would be a one-and-done thing. He’d bottom once, then go back to topping because it didn’t matter. He was still a damn good top and that wouldn’t change with one little dip.

He needed some liquid courage, though, before he made the call to Gabriel. His drive to and from the liquor store was slow and subdued, putting off the inevitable. He didn’t know why he was nervous. He was fine. Agan, it wasn’t a big deal. Just a one-time thing. One video. He’d done some crazy shit, this was nothing. A roll in the hay and a paycheck. Nothing to worry about.

He drank slow but he drank enough. He was about an hour in when a little buzz took him on, and another hour when that buzz became a real loud hum.

“Hey, Gabriel,” Dean slurred into his phone, and when had he picked that up and started a call? “I’m gonna do it. We’re going at 75k and I get an extra 500 bucks unless you let me pick the guy. That alright?”

Gabriel was silent for a moment, but he spoke soon enough. “500’s in your bank account; we’re going with my guy. You’re 100% on this? Because you can back out, but it’s kinda gonna suck if you do. I want you to be sure, here.”

Dean nodded, even though Gabriel couldn’t see. “Yeah, I’m serious. A little drunk so I wouldn’t be nervous, but I made the decision before I had anything in my system. I’m not gonna back out but I know I can. I’m too stubborn for that, though.” The two of them both chuckled a little. “I’m gonna regret how open my mouth is later, but whatever. I’m in this, promise. 75k’s a ways away. Whoa, that rhymed.” Dean laughed again. “Say that five times fast. K’s a ways away, k’s a ways away, k’s a wezzuh weh… I can’t do it.”

“Alright, silly goose,” Gabriel laughed. “I’m gonna leave you to it. Be safe, alright? Don’t drink any more or you’ll pass Giggly Street to Miserable Town and wake up in Hangoverville.”

“I’m gonna stay home,” Dean decided.

“Atta boy,” Gabe praised. “I’ll talk to you later. Bye, Dean!”

“Later,” Dean said, and Gabriel hung up in his ear. He promptly crawled up off the floor to lay down on the couch and pass out.

 

•°•°•°•°•°•°•°•

 

The girl in charge of costumes, Anna, was beautiful and sweet. Dean may have gone for her at some point in any other situation, but he didn’t feel it appropriate. Plus, she was clearly interested in other things.

“...So I called Charlie, and she wouldn’t even answer. I felt so bad,” Anna continued on her story, talking away as stabbed another cherry tomato with her fork. “I think we’re okay today, though, because I’m still bringing her food tomorrow.”

“That’s good,” Dean said, trying to sound interested and calm simultaneously.

“Definitely,” she agreed, muffled around a bite of salad. Anna just didn’t give a fuck sometimes. Dean liked that about her. “Speaking of good, hot damn. Your skin is constantly clear, you have a gorgeous body, your freckles are adorable, your eyes are beautiful, your lips-“

“Anna,” Dean complained.

“I know, I know,” she said. “Poor little Michael, doesn’t know how to take a compliment. Boo-hoo.”

“I don’t like your tone,” he muttered.

“And I don’t like that your ass is hotter than mine and my girlfriend’s combined.” Dean snorted, and she grinned with him. “You never know, maybe you’ll be using that hot ass more than just this once.”

“I doubt it.”

“I don’t,” she laughed. “You’ve got no idea what you’re in for.”

“What do you mean?”

“Your co-star. Do you know who he is?”

“I, uh… Actually, no,” Dean said.

“Of course Gabriel forgot to tell you his name,” Anna scoffed. “You, my friend, are gonna get plowed by the one and only _Jimmy Novak_.” She grinned at him, wide and excited. Something must’ve shown on his face, though, because that was quickly replaced with shock. “No way. You don’t know who he is, do you?”

“Should I?”

“Should you?” she repeated, as though that was the dumbest thing he could’ve possibly said. “Michael, of course you should. He’s a legend. He’s basically the gay porn equivalent of Belladonna.” Dean cringed. “You don’t know who Belladonna is.”

Dean shrugged sheepishly. “I know Michael Sword and that’s about it.”

“Oh my god. You’re ridiculous.” She scoffed and started putting her lunch mess into a bag, talking while she did so. “I’m not even gonna bother filling you in, because you should know this already by now. Plus, you’re gonna find out today anyway.” She looked right up at him, a devious spark lighting her eye. “I think you’re gonna be pleasantly surprised.”

Whatever that meant.

“Oh, and Michael?” she said, innocence in her voice. Dean could see right through it.

“Whatever it is, just fuckin’ say it,” he griped.

“You’re gonna have to do an enema,” she grinned. “I’ll walk you through it, but I’m pretty sure you’d rather do this yourself, yeah?”

Dean groaned into his hands, then ran them through his hair. “Fucking hell.” He shook his head a few times, trying to clear away all the thoughts of _nope nope nope_. “Okay. Okay, I can do this. It’s not bad, right?”

“It’s not bad,” Anna agreed. “It can be uncomfortable, especially the first time, but it shouldn’t hurt.”

“The first and _only_ time,” he corrected.

“Of course,” she said, clearly just to soothe him. Dammit, why did everyone assume he wasn’t a top? “Come on, bud, let’s go clean that peach. Ooh, should we shave you too? Don’t answer that. You’re gonna say no, but I totally wanna shave you. Gabriel will agree anyway, so don’t fight this.”

“Oh my god,” Dean complained. “I already shaved, I’m not gonna have more than one person pawing at my ass today.” He thought back to the enema thing, and god he hated that. “You know what you’re doing, with the cleaning thing, right?”

“I literally do this for a living,” she soothed. “You’re in good hands. Good, intelligent hands.” Dean was fucked. He followed her down through halls, all the way to some sort of salon-bathroom hellspawn. He sat on a table when she gestured for him to do so, and noted that it was covered in a sheet of plastic. Great.

“I hate this,” Dean informed her. Anna just grinned and grabbed a bowl, cleaning it out with some fancy sanitizer, then filling it up with steaming water.

She turned back to him, now holding both the bowl and an enema. “Alright, sweet cheeks. Pants off.” Dean winced but did as he was told.

The whole process was mortifying, but not at all painful or even as uncomfortable as he expected. The worst part of the enema was his own nerves and the gross feeling of it, though he could admit a lot of that was mental. She had left the room for it, thankfully, even going so far as to instruct him via text instead of listening in through the door. Didn’t make it better, honestly.

She was good about it though, making jokes to ease the tension while still being as direct as she needed to be. Anna was good about that. She was good at making him feel comfortable during all the weird awkward scenes he had to shoot. Although her real talent laid more in her ability to make him look decent when he knew he looked like shit. He usually tried to get a good night’s sleep in the night before a shoot, to be sober, to take care of himself, but he had abandoned all of that last night in favor of wallowing in nerves for a while.

His expectations were low. This was going to fucking suck.

 

•°•°•°•°•°•°•°•

 

When Dean first met Jimmy Novak, he was genuinely surprised. When he’d been told he was going to be hooking up with some sort of dom-top legend, he’d been expecting a huge hairy bear of a man. The guy sitting on the couch was muscular, yeah, but clearly not from steroids or anything like that. He had an attractive layer of stubble on his face and a strong jaw. His thighs looked powerful, and this hands, _fuck_ , his hands.

“Dean!” Gabriel called. “I was just getting Cassie here all set up. You ready to rumble?”

Dean suppressed an eye-roll, replacing it with a curt nod. After the whole enema debacle, to say he was discouraged would be an understatement. He sat next to the other porn star, giving him a courteous smile. May as well try not to be a dick about this.

“Dean,” he offered, but only received a confused look in return. “I figure since I now know your real name is Cassie, you should know mine too.”

“My name isn’t Cassie, Gabriel’s just a dick,” he corrected. “I’m Castiel. It’s a pleasure to meet you, Dean.” He locked eyes with Dean, then pointedly dragged his eyes up and down his body. “I must say, you’re more attractive in person. That’s saying something.”

Dean grinned, already feeling a bit more in his element with a guy calling him hot. “I also feel better in person.”

“Is that so?” Castiel smirked, a dark look bleeding into his eyes. “My expectations are rather high.”

“Save it for the cameras, ya damn horndogs,” Gabriel protested, and Dean’s budding arousal rushed out of him like a whoopie cushion. The director’s interruption clearly had the same effect on Castiel, because he visibly deflated as well. They both turned their eyes to Gabriel, who was signaling to one of the cameramen to start recording.

When the dude gave Gabriel a thumbs-up, the man spoke up again. “Alright, we’re gonna jump on into this now. Michael Sword and Jimmy Novak, you guys are two of the biggest names in the game. Fans have been demanding you two scene together for years, and they’ve been demanding Michael bottom on camera for years. Here we are! Are you guys excited?”

Castiel took the torch, thankfully. “I totally am,” he confirmed. “I mean, god, have you seen him?” Dean grinned and lightly hit his shoulder, and Castiel smirked right back at him. “How about you, Michael?”

He paused for a moment before saying, “I think it’s gonna be interesting.” 

“That was hesitation right there!” Castiel laughed. “You think you’re not gonna like it?”

“I mean, yeah,” Dean blurted. He only had a split second to be worried about bothering the other man, but instead his response was met with laughter. He smiled and continued. “No offense to you, man. I’m sure you’re great, but I’m a top.”

Castiel gave the same sexy smirk he had before. “Oh, you really think so, huh?”

“Don’t get ahead of yourself there, Jimmy,” Gabriel warned. “Michael, you’ve never bottomed, is that right?”

“Yeah,” he confirmed. “It’s, uh, it’s a one way street.” All three of them laughed after that, though Dean was ultimately more tense in his.

Gabriel continued, leaning in a bit. “So you’ve never even played with yourself?” Dean shook his head. “Haven’t you had the thought?”

He shrugged. “Sure, I’ve had the thought. But no, I’ve never put anything inside myself. Cleaning out earlier was uncomfortable, so I can’t imagine fingers would be much better.”

“You’d be surprised,” Castiel promised, voice deep and seductive in Dean’s ears. “Pleasantly, blissfully surprised.”

“That definitely brings up a nice question,” Gabriel added. “Michael, have you heard anything about Jimmy from the actors that have worked with him?”

Dean looked at Castiel, unsure what he was trying to gather from the man’s face. Castiel grinned at him, which didn’t help much. “No, actually. You got a reputation?”

Castiel chuckled. “I’d like to think so,” he said, ignoring it when Gabriel scoffed. “Guys are usually far more excited to scene with me than you are. I hear Alfie brought Gabe a box of chocolates and a thank you card.”

A laugh bubbled out of Dean’s chest. “I call bullshit, but I’m sorry to disappoint either way.”

“Oh no, don’t be. I look forward to making you beg for me.”

“Not gonna happen,” Dean insisted, but he felt a part of him melt anyway.

Castiel leaned in slightly, eyes dark. “Oh, ye of little faith.”

Gabriel interrupted their sexual tension once more. “You guys sound like you’re gonna have a bit of a challenge on your hands. I’m gonna say it right here, on record, I’m docking your pay if you fake anything. Jimmy’s gonna have to work for it if he wants you to react.”

Dean blinked a bit, but recovered quickly. “I don’t think I’m gonna have a challenge there, in that case. I can deal with anything,” he said, then grinned before continuing. “I’m just gonna need to pound a few twinks to cleanse my system after this.”

Castiel laughed, then spoke himself. “To contrast, I also don’t think I have a challenge here. I’m gonna have no problem getting him desperate for me.” Dean nearly rolled his eyes.

Gabriel smiled, even though the camera was only focused on the couch. “I guess we’ll just have to wait and see. I don’t know about you, but I’m genuinely excited for this. I think it’s going to be a lot of fun.”

“Ditto,” Castiel grinned.

“I didn’t before, but now I do,” Dean agreed. “I think I’m gonna have a good time proving him wrong.”

Castiel laughed darkly, shaking his head, and Gabriel yelled for the cameras to cut.

 

•°•°•°•°•°•°•°•

 

Dean sat on the soft bed and tried to hype himself up a bit while the cameras were getting ready. He was a professional, this was nothing. He would never bottom in his personal life, where it really carried risks; if nothing else, it was cool that it was a safe environment. If he had to call it off, they had things in place so it wouldn’t affect him negatively.

He saw Castiel off to the side, talking to an assistant and laughing. The man was legitimately good-looking, and Dean probably would’ve fucked him if he bottomed. Come to think of it, he didn’t know if Castiel bottomed. A part of him wished Castiel was the one in his place, about to get his ass reamed by Dean fuckin’ Winchester.

It seemed like time went by way too quick. All too soon, set was ready and the cameras started to roll. The opening shot was supposed to be Dean on the bed wearing only some tight boxer briefs, showing the vague half-tent he was rubbing. That was all he’d been told about the scene, the rest was supposed to be a surprise. 

Castiel walked in from one side, grinning. “Come here often?”

Dean chuckled and grinned too. “Shut up and kiss me.”

“Feisty,” he joked, but climbed onto the bed over Dean anyway. The kiss was gentle, the two of them feeling each other out for a bit. Cas ground down against his leg after a moment, before shifting his hips and grinding their cocks together through their boxers. Dean sighed into the kiss, suppressing the stage moan he was trained to let out.

He felt himself melting a bit up until Cas smiled, and he remembered why he was here. He wasn’t going to give Cas the upper hand. In one swift movement he rolled them over, then connected their lips again. Cas laughed and didn’t try to fight back, just went with it. Dean ground into him, the way he knew was hot as hell. His back, his legs, his arms, everything about his movements was sleek and dominant. His confidence rushed back to him at the mental image of himself.

Cas only let out a soft grunt, which Dean had to admit was a bit disappointing. That specific hip roll usually drove people wild. He didn’t have time to think about it though, as hands moved from his shoulders to feel around his body. One roamed across his back, feeling along his muscles. The other rose up to his hair so Cas could run his fingers through it, and damn that felt nice. Dean had a bit of a thing for having his hair pulled, but a gentle touch was definitely nothing to complain about.

Actually, no. It was something to complain about, considering the whole dynamic they had going on here. Dean bit down on Cas’ lip and taunted, “I thought you were supposed to be the big bad top, huh? Can’t keep up?”

Cas didn’t take the bait, surprisingly, laughing instead. “I don’t need to keep up, Dean. If you think this is what you’ll like then we can go for it. I can make you scream whether I fuck you or you ride me.”

Dean ignored the part of him that was turned on by the dirty talk, instead focusing on the part of him that took it as a challenge. “If you think I’m gonna make it easy on you, you’ve got another thing coming.” Cas grinned and seized up to kiss him again, dominance soaking through it. Dean fought it, giving as good as he got, and he was sure it had to look fucking hot on camera. Tongue and teeth and all fucking rough, because he didn’t know about Cas but he definitely wasn’t trying to take it easy.

Dean unfortunately lost, though, because Cas was a fucking dick. The hand resting in his hair suddenly pulled at it, not to yank him away but just to give him the sensation of pleasure-pain. “Fucker,” Dean spat, and he hoped it sounded less high-pitched on camera than it did in real life. He met Cas again, trying not to lose himself in that stupidly talented mouth. The hand in his hair stayed, petting through it in apology. The other one, though, moved around again. It traveled to his chest between them and twisted his nipple, and the twitch of his cock reminded Dean that they were still grinding together.

He honestly started to wish Cas would get this over with. He’d been prepared for the cocky son of a bitch in the interview, not the boring one he was apparently going to get. Insults didn’t work, the kissing thing didn’t work; the man didn’t crack.

It became very clear that nothing worked about the same time that both of Castiel’s hands removed themself from Dean’s body, only to collide sharply in matching slaps on his ass. Dean arched away from it, an embarrassing sound leaving him. He knew that didn’t sound like a grunt, that’s the kind of noise Dean gets out of other guys. Fucking hell.

The slaps were followed by hands squeezing his cheeks roughly through the boxers. Dean kinda had a love-hate relationship with them. They were protecting his dignity, but he really wanted to be skin-on-skin here. He decided to give up on it, pulling away from Cas’ mouth to look him in the eyes and pull the man’s cock out of his underwear. He stroked it slow and tight like he would his own, not like he would usually do on a partner.

Cas seemed to appreciate it, judging by how he almost immediately started a gentle rhythm meeting Dean’s hand with his hips. He pulled Dean’s boxers down too, but only down his ass. Dean wanted to yell at him, but he settled for firing rage through his face and hoping it translated. It did, it Castiel’s shit-eating grin meant anything.

The hands on his ass really went for it, pulling him in and squeezing a bit rougher. He wanted to make a noise, but he didn’t want to risk embarrassing himself again. He didn’t get the opportunity to have face, though, because he soon felt his cheeks being spread for the camera. “What, baby?” Cas cooed. “Don’t like showing off how pretty you are?”

“Shut up,” Dean snapped. He rolled them over again so Cas wouldn’t have another opportunity to pull that shit. Cas immediately took advantage of it, wrapping Dean’s legs around his hips and taking over the kiss again. Dean didn’t fight the positioning, deciding that it at least gave him a bit of control if he used his legs.

An added benefit was that Dean could get Cas back. He tried to be subtle, distracting Cas with his mouth and curling his legs up around his waist. He ran his hands down Castiel’s back and used his legs to push their cocks together, now bare against each other. Fuck, it was nice, especially when Cas reached a hand down to wrap around them both. Dean ran his hands further and further down until he finally reached the other’s boxers. 

Focused as he was, he jumped minutely when Cas spoke. “You can do anything you’d like, but you’re still taking my cock today.” Dean scoffed and slapped his ass as a test, getting no physical response. “Not that I mind, but I think I should start getting you ready to take my cock. You said you’ve never had anything in there, so it’ll be uncomfortable at first.”

Dean grunted, not wanting to give any sort of real response, and let his head fall back onto to the pillows while Cas plucked the lube from the (prop) nightstand by them. “You can stay here, but it’ll hurt less if you’re on your hands and knees.” Dean knew that; he’d said the same thing to a ton of other guys, as well as a few adventurous girls. He nodded and untangled his limbs so he could roll over. He felt Cas scooting back to give him room, and with one last deep breath to steel himself, he raised himself up with his ass in the air.

Oh boy. Dean Winchester, about to take it like a bitch. Look at him now, a true fairy.

He jumped when a soft hand touched his shoulder blade. “Hey,” Cas soothed. “You’re okay. You can say no at any time. You don’t have to do this if you truly don’t want to. Nobody will be mad at you. If they are, then they can go fuck themselves… to something else, that is.”

Dean chuckled a little despite all the negativity flowing through him. Could be worse. They could’ve paired him with some dick that didn’t give a shit. “I’m good,” he said, but it came out as a croak. “I’m good,” he repeated. “Just gimme a sec. Need to stop freaking out here.”

He looked over his shoulder at Cas, who was smiling softly. “Yeah, you’re good,” he said. “They can cut all this shit out, and we can just talk for a while if you need it.”

“Hell no,” Dean said, getting back to himself and grinning. “This whole hatefuck dynamic? That’s gonna be hot. I don’t wanna know you, I wanna make you go home with your tail between your legs because you couldn’t top me good enough.”

Castiel laughed heartily. “If you say so, Michael.” Dean chuckled too, and leaned up to kiss him again. He allowed himself to relax into it, trying to see it as less of a pride-blow and more of a game. “You ready?” Cas whispered, and Dean felt a gentle hand pulling one of his cheeks.

“Yeah,” he said, a little breathier than he was maybe hoping for. Cas kissed him deeply and circled one lube-slathered finger around his hole, gently feeling around and letting him get used to the idea of sensation there. Dean could feel himself slowly untensing, and he nodded after a minute.

A soft finger entered him, slow and sure, until the first knuckle rested just past the tight ring. He flinched a little bit, because that was definitely not comfortable. He suddenly felt bad for all the times he’d been a little rushed with it. He fell back to his hands, trying to make the angle easier, but the sudden twist of the finger was a sharp sensation somewhere between _ow_ and _what the hell_.

He must’ve hissed, because while the finger stayed, a hand was on his shoulder again. “C’mon, Michael,” Cas cooed. “You got this, little hatefuck.” Dean laughed a little at that, and wow, laughing with a finger in your ass was another weird feeling. Jesus, this whole thing was not as fun as bottoms made it out to be.

He took one deep breath before he nodded again, muscles as relaxed as they were gonna get. Cas pushed the rest of his finger in, slow and smooth, until Dean could feel knuckles against his perineum. It wasn’t bad, necessarily. It didn’t hurt, it just felt… different. Not great, obviously, but not the worst. “Move it,” he said, a little cautious. Sure enough, the finger was slowly pulling out, and wow, that was not very good at all. Not painful, but the sensation of something leaving that zone was not his definition of sexy.

“I kinda hate this,” he blurted, before his mind could stop him. Cas snorted his way into laughter, his finger blissfully still. “Shut up,” Dean barked. “It’s a weird feeling!”

“I know,” Cas gasped. “I know, I get it. It’s just… I’ve definitely never heard anything close to that in times like this.”

“Coulda fooled me,” Dean sassed, and the finger plunged back into him in retribution. He let out a little noise, more out of surprise than anything else. Once again, it wasn’t painful, and this time it also wasn’t that uncomfortable. He felt like his body was getting used to it, thankfully. “Get on with it, man, I’m not fine china.”

“I mean, yeah,” Cas said. “Ass this nice? You’re plastic for sure.”

“Eat my ass,” he barked, until his brain reminded him of the position he was in. Great! Irony was really on his side today.

“Don’t mind if I do,” Cas purred, fucking his finger in and out a little faster.

Dean shuddered, though he couldn’t identify why he did. He’d cleaned out and everything, so it wasn’t like it was particularly gross. He’d been on the other side for his job, and it wasn’t the worst thing in the world. It was always really fake though, exaggerated moaning from both sides and moving your head around weirdly for the camera. Before he started acting, back when he was just a broke college kid jacking off in his dorm, he would always skip those scenes in the videos he watched. 

“What do you say, Michael?” Cas asked. “I’ll admit I’ve been wondering what you taste like since I first saw your pretty ass.”

“You can’t tell me you actually dig it,” he said, voice as baffled as he felt.

“I won’t say whether or not I have an affinity for it, because that’s not relevant,” Cas said, pulling his finger out and positioning himself more directly behind Dean. “I do, however, love the way I can make my partners fall apart through it.”

Dean had to admit, he was kinda curious. It’s not like he’d ever bottom again, so he may as well check all the marks off. He gave Cas a skeptical look but told him, “Go for it.”

Go for it, Cas did. He dove in and immediately spread Dean’s cheeks, licking one long stripe from Dean’s scrotum to the top of his crack. He went back down then, laving hot stripes over his hole. “Jesus,” Dean hissed. It felt more sensitive to Castiel’s tongue than it did his finger. Cas kissed it, filthy and open-mouthed, and fuck, Dean had never even thought to do that to anyone. 

Cas hummed against him, and that little vibration sent shockwaves up his spine. His first real moan of the day made its way out of his chest, and he could feel the pride coming off of Cas. Almost in praise, the hands hold his cheeks squeezed a bit, and the tongue licking over him dipped inside a bit. Fuck, Cas was good at this. It actually felt really good. Like, _real_ fucking good.

“God, Jimmy, you really love this, don’t you?” he asked. His voice was breathless and higher-pitched than usual, and he was more than a little proud of himself for remembering to call Cas by his stage name instead of by his actual name. “You’re not just- ngh- just doing it for the cameras.”

“God no,” Cas said, pulling away. He sounded as though _he_ was the one receiving pleasure. “Everything here’s completely real. Just like you’re completely loving this, despite how much you’d like to pretend you’re not.”

“You can shove your ego up your-,” Dean cut himself off on a gasp when Cas’ finger found its way inside him again. His arms trembled where they were holding him up, and he hoped that wasn’t visible on camera.

“My what?” Castiel teased. “My co-star’s ass? Because if we’re referring to my dick as my ego, I think I’d be offended. My heart is bigger than my balls, you know.”

“Do you ever shut up?” Dean groaned, feeling his anus spasm around Cas’ finger.

“Not when I’ve got a pretty thing like you in bed,” Castiel purred, diving back down to lick and suck around his finger. Dean let out a little hum and his left hand finally gave up, dropping him abruptly to his elbows. He yelped as the finger inside him was forced to compensate for the change in angle.

“Sorry. Are you alright?” Castiel asked, breath hot against his ass.

Dean nodded. “Yeah, just surprised me. You can keep going.”

“Mmm, how I wish you’d let yourself beg,” Cas said. “You’d be so gorgeous. I’m gonna add another finger, so just stay relaxed.”

Dean knew to stay relaxed, so he kept his breaths steady when he heard the lube click again. Cas pulled the first finger out and soon there were two easing in. It wasn’t… bad. It wasn’t anything difficult to take. There was a bit of a burn, but it was almost comfortable in a way. His body had become familiar with the feeling of being open, and he wasn’t hating it. It didn’t feel magical by any means, but he could put up with this.

It was nothing like the other way around though. The feeling of being full was incredibly different than the feeling of filling. “Touch me,” he insisted, almost reflexively. He wanted something on his cock.

“We’re getting there, baby. Patience.” Castiel's voice was strong and deep in his ear and Dean found himself losing focus. The fingers in him were sliding in and out, steadily pumping away. Cas kissed him and spread his fingers at the same time, causing Dean’s tiny moan to be swallowed immediately. Cas whispered, rough and hot, “Want you so much.”

Dean nodded, mind slowly leaving as is focus became solely on pleasure, on that satisfyingly full feeling of Cas’ fingers opening and twisting slowly, oh so slowly and-

“Fuck,” he cried, body jolting. Cas chuckled in his ear and bent down to kiss at his shoulder. “Again.” Cas obeyed, moving his fingers to rub at his prostate again. Jesus christ, this was good.

All too soon those fingers stopped working wonders in him, and he was empty. “Roll over,” Cas demanded, dominance easily falling into his voice. Dean did, head falling back into the pillows and a bit of his mind coming back to him. “Good boy,” Cas praised, leaning down to connect their lips again.

Dean moaned into it, wrapping his limbs around Cas and pulling him in close. Their dicks met and _fuck_ Cas was wet, precum leaving a hot trail against Dean’s stomach and cock. He wanted to taste it so fucking bad. He always loved sucking guys off, taking them deep in his throat and staying until he couldn’t take it.

It apparently wasn’t in the cards, unfortunately. The fingers from before entered him again, slathered in more lube and stretching more than teasing. This wasn’t just getting Dean hot for it, this was to get him ready to be split open on Cas’ dick. Fuck, he wanted that.

He whined, muffled by Castiel’s tongue in his mouth. “Please,” he moaned, not knowing what he was asking for. “Jimmy, please.”

“I’ve got you, sweetheart,” Castiel said, and it sounded like a promise. “Are you ready for me? Want me to fuck you?”

Dean dropped his head back to the pillow and decided to make a fuck-it adjustment on all the things that were hesitating about this. He nodded, and felt a grin fall over his face as all the repressed enjoyment seemed to rush over him. “Yeah. C’mon, fuck me. Unless you’re all talk? I mean, I’m still totally willing to switch this around. Wouldn’t be the first time I’ve had somebody all needy for me.”

Castiel chuckled, apparently seeing Dean’s teasing for the camera tease that it was. “I think you’ll be quite fond of my talk, Michael. I’m rather known for it.”

“Good,” Dean breathed, glancing down to see Castiel’s hand on his own cock, slathering it in lube. It was a bit of an odd thought, but the dude had a really nice dick. Thick and long with a nice vein running along the side. It curved slightly up, and the head was smeared with the same precum he’d left all over Dean’s stomach.

Cas leaned in to kiss him again, but Dean only let it last for a moment. “Wanna watch,” he explained as he pulled away. Cas nodded and a little smile fell over his lips. Both of their eyes turned down to watch Cas line his cock up, then slowly try to push its way in. Dean remembered all at once to bare down and sure enough he opened up around the head.

Fuck, there was a cock in him. There was a cock slowly sliding into his ass, opening him up and stretching him out. It wasn’t good or bed yet, just full. Actually, no. No, that wasn’t good.

Castiel stopped at the sound of his hiss. “Sorry,” he winced. “Want me to pull out?”

Dean shook his head, not trusting himself to speak. His eyes had clenched shut at some point, but he pried them open to look at Cas. Were his eyes that blue before? They were seriously gorgeous, a pool of sky blue surrounded by a pool of navy blue. They looked like perfect sapphires, broken up only by the dilated pupil in the center.

Dean’s breath hitched when Cas moved again, slowly sliding himself further in. Dean could feel it, could feel every inch stretching him open a little further. His mouth hung open limply, shallow breaths making their way in silently and out in soft moans. The whole idea of this was sex, but this wasn’t at all like topping. He felt empty and full, tight and stretched, too much and not enough. He couldn’t place himself in any one sensation, there was so much, god, so much…

“Look at me,” Castiel whispered. Dean was. He was looking, right? “Come back, baby. Look at me.” Dean’s breath came out in one heavy puff, and all the tension in him released. He could feel sharp hip bones resting against the backs of his thighs, which meant that Cas had apparently gone all the way in. Dean clenched down a bit just to test the sensation and wow, that was a lot. “Good boy,” Castiel praised. “You ready for me to move?”

Dean nodded, but the other still hesitated. “Fuck me,” Dean insisted. “I want you to fuck me.”

Apparently that was what he’d needed, because Cas moved almost immediately. He pulled out, smooth but careful, until the crown of the head was tugging at Dean’s rim again. The thrust in went easier, as did the one after that. It didn’t take long for Cas to build a rhythm, his hips rolling steadily. Cas paused for a moment and moved his knees a little higher up the bed before-

“Oh god,” Dean gasped. The slight change in angle had the shaft of Cas’ cock rubbing up against his prostate and fuck, that felt good. He needed something but he didn’t know what. Cas was moving again, picking up the same pace as he had before, but it wasn’t enough. ”Faster.” It was obliged right away, Cas’ hips moving quicker and his cock constantly filling Dean up.

“You like that?” Cas growled. God, Dean had forgotten that the guy was so damn cocky about this. It was playful before but it was driving him crazy now, melting him a little bit and making his cock leak onto his stomach. His only response was a pitiful whining sound he didn’t even know he was capable of making. “Feels good, doesn’t it?”

Dean could feel himself nodding on instinct alone. “Please,” he begged, but he had no idea what he was even asking for. “Please, fuck, please.”

“What do you want, baby?” Cas teased. “Want more? Wanna be fucked hard?”

“Yes, need- _oh fuck_.” All of a sudden it got exponentially more intense; deeper, faster, harder, and fuck, Dean felt like he was losing his goddamn mind. “Oh my god, oh my god. Fuck. Oh jesus, fuck.”

Castiel’s answering chuckle was hoarse and breathless in his ear. “Told you that you were gonna be a slut,” he rasped. “Knew you were, so big and tough. Just need to be filled up like a good boy, huh?”

Dean could barely hold his legs up around Cas’ hips anymore, so he reached a hand up and put it on the man’s chest. The thrusts tapered off and a questioning look was leveled on him. Cas’ eyes still held hunger, dark and demanding, and it was clearly hard for him to stop. Dean shuddered and wriggled away until Cas slipped out of him. He immediately turned over, flopping onto his stomach before lifting himself up onto his knees. “Like this,” he said.

Cas groaned behind him, and hands quickly fell to wrap around his hips. An insistent pressure returned right back at his entrance, and he was filled back up in one swift movement. He and Cas both groaned at the same time, and Dean’s fingers curled up into the sheets. Yeah, he liked this position a _lot_.

Fingers dug harshly into his hips as Castiel fucked him harder than he had before, pistoning in and out almost viscously. Dean let out one long moan, the constant stimulation nearly too much to handle. Every thrust in jostled it, leaving behind a series of little “ _ah-ah-ah-ah-_ ” sounds one after another. A tear slid down his cheek when Castiel paused to give a series of dirty little grinds that put him as deep as possible, stretching Dean open further where he hadn’t been before. Fuck, this was so good.

“Such a good little slut,” Cas praised. “Good, needy little bottom. Always needed a cock in your ass, you just didn’t know it, hm?”

Dean couldn’t respond; he could only really focus on the feeling of his orgasm building, stopping _right there_ before it could go all the way. He needed something, fuck.

“Please, please, I- oh,” he moaned. “Wanna come. Need- need to come, please. Lemme come.”

Cas growled, “Make yourself come. Touch your cock.” A hand moved from Dean’s hip to wrap around his chest, and a swift movement pulled him upright with his back to Cas’ chest. The other hand came up too, then, and two fingers slid in between his open lips. “Suck them,” he demanded, but Dean had already wrapped his lips around them anyway.

When his hand wrapped around his cock, his head fell back onto Castiel’s shoulder. A wrecked whine bubbled out around the fingers in his mouth, and Dean desperately jacked himself. Tears streamed down his face when he came, his entire body shaking and his muscles tensing. His cock spasmed with every pulse that left it, painting the headboard with long streams of white. He fell limp when it was over, running his tongue over the indentations of his teeth that he’d accidentally left on Cas’ fingers.

“Such a good boy,” Cas praised, thrusts quickening and pushing Dean closer to the line of oversensitivity. A hoarse moan left him, but Castiel ignored it in favor of speaking again. “So hot, coming on my cock. So fucking gorgeous.” He laid a sucking kiss on Dean’s shoulder, then followed it with a bite. “I’m close too, baby. Want me to come?”

“Yeah,” Dean mumbled around the fingers. “Come inside me.”

Cas’ groan was rough and dirty, and he sped up. His grip tightened on Dean’s jaw and on his chest, and the harsh smacking of his sharp hips against Dean’s ass was practically bruising at this point. “Fuck,” he moaned, and his head fell forward onto Dean’s shoulder. “Fuck, so fucking good. I- _shit, oh fuck-_ ”

Dean could feel Cas’ cock twitching in him, could feel the balls tightening and releasing right up against his ass. His own cock tried valiantly to join the party, but he was definitely out for the moment. All he could do was push his ass back against Cas, a silent request to fill him as much as he could.

They stayed upright for a moment after Cas’ orgasm eased up, but Dean could feel both of them trembling. Dean rolled away onto his back, and Cas quickly flopped down onto his stomach in the space Dean had left. It was silent for a bit, but Dean felt a laugh bubbling up out of his chest when a drop of cum leaked out of him.

Cas popped his head up and gave him a confused squint. It only served to make Dean laugh harder, pure joy flowing out from him in a cascade. Cas still looked confused, but he chuckled too, likely just some visceral reaction coming through.

Dean rolled over, still grinning, and laid a kiss on his lips. Cas kissed him right back like it was something they’d been doing forever, like he knew everything about Dean. Maybe it was endorphins or something, but Dean felt his heart swell up a little bit.

He vaguely heard Gabriel calling for a cut, but if Castiel didn’t stop kissing then he wasn’t going to either.

 

•°•°•°•°•°•°•°•

 

Dean ignored the butterflies in his stomach when Cas pulled him in to sit on his lap. There was a lot of couch space, Dean could’ve protested, but he really fuckin’ loved it. Cas was seriously awesome. He was quick-witted and had a dry sense of humor, but once he caught onto Dean’s love of puns he kept a steady stream of them going while they’d got cleaned and dressed together.

Not to mention he was hot as hell.

“You two look rather chipper,” Gabriel commented once the cameras had begun recording.

“I’m doing pretty well, myself,” Cas said, and Dean could hear the rumble of his voice straight from his chest. “How about you, Michael?”

“Fucked out,” he said with a lazy grin. “Jimmy’s a damn good lay.”

“So you liked it?” Gabriel asked. “Good first bottoming experience?”

“Yeah,” Dean agreed. “I mean, it felt kinda weird sometimes, but he was good to me.” He didn’t need to see Cas’ face to know he was preening.

“Can we expect to see you bottoming again?”

Dean thought about it for a moment, until one little idea popped up and blasted away all other thoughts. His face flushed, but he made himself say it anyway. “I think I’d bottom for him again. I dunno about anyone else.” Castel’s responding chuckle danced around his chest, light and sweet.

“I think we can make that happen,” Gabriel promised. “Jimmy, you’re interested in that, right?”

“Of course,” he confirmed, like it was a no-brainer. “This is by far the greatest scene I’ve ever done.” Dean pulled back to look at Cas with wide eyes, and got a smirk in return before the man continued. “I was actually going to ask Michael if he’d like to continue something with me outside of the studio, and maybe even outside of the bedroom.”

Dean let out a tiny squeak, and Castiel’s grin widened. “I- uh,” he stammered. “Yeah. Uh, yeah. That- that sounds good. I’m- uh- interested. In that. Yeah.”

Castiel and Gabriel both laughed, and Cas kissed the top of Dean’s head while Gabriel spoke. “I’m an incredible matchmaker. I should do this for a living. Oh wait, I do!” Dean snorted at that. “I’m glad you guys had so much fun with this, I definitely think it turned out great. Michael was made to bottom.”

“Hey!” Dean cried, but Castiel was nodding above him. He slapped the man’s chest in retribution, his face heating up again. “You’re both asses.”

“You are what you eat,” Cas mumbled, and Gabriel laughed way harder than Dean thought necessary.

“I would appreciate it if you were to shut up forever,” Dean grumbled.

“Can’t talk with your tongue in my mouth,” Cas offered, and Dean’s grumpiness fell away. He grinned at Cas and pulled him in for a sloppy open-mouthed porn kiss that was totally for the cameras. “Trah hahduh,” Cas mumbled into his mouth. Dean internally rolled his eyes but stopped playing it up, actually closing in on Cas and kissing to make him melt.

When Cas’ hand snaked over into the back of his boxers, that was apparently too much for Gabriel. “As much as I encourage you to fuck like bunnies on camera, we kinda need this couch to stay clean.” Dean flushed and tried to pull away but a hand on the back of his head stopped him, and a finger pushed into him. Cas kissed him furiously, and a touch on his prostate had Dean forgetting why they were supposed to stop. He gasped into Cas’ mouth and Gabriel scoffed. Gabriel yelled “Cut!” right as Dean forgot to moan Castiel’s porn name.

Dean was fucked, so fucked, and he couldn’t get enough.

**Author's Note:**

> I hope you guys enjoyed this! Comments and kudos are loved and appreciated, I'm thinking of writing more in this 'verse so let me know if that's something you're interested in, and maybe some ideas you might wanna see! Kinks you want them to try out, behind the scenes, Sam's reaction to Dean's porn star life, whatever you guys are interested in. I want to consume your thoughts.
> 
> On that note, you can [click right here](https://giddyupdean.tumblr.com/post/184548162989/) for a lil timestamp drabble I wrote about this fic!


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